NO300445B1 - Kompleks omfattende et pleuromutilinderivat og farmasöytisk preparat omfattende dette kompleks - Google Patents
Kompleks omfattende et pleuromutilinderivat og farmasöytisk preparat omfattende dette kompleks Download PDFInfo
- Publication number
- NO300445B1 NO300445B1 NO922901A NO922901A NO300445B1 NO 300445 B1 NO300445 B1 NO 300445B1 NO 922901 A NO922901 A NO 922901A NO 922901 A NO922901 A NO 922901A NO 300445 B1 NO300445 B1 NO 300445B1
- Authority
- NO
- Norway
- Prior art keywords
- cyclodextrin
- complex
- formula
- compound
- complexes
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 229920000858 Cyclodextrin Chemical group 0.000 claims abstract description 52
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical group O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000003839 salts Chemical group 0.000 claims abstract description 24
- ZRZNJUXESFHSIO-VYTKZBNOSA-N pleuromutilin Chemical class C([C@H]([C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-VYTKZBNOSA-N 0.000 claims abstract description 15
- 239000012458 free base Substances 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 12
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 8
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 abstract description 8
- 239000003242 anti bacterial agent Substances 0.000 abstract description 5
- 229940088710 antibiotic agent Drugs 0.000 abstract description 4
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 4
- -1 pleuromutilin compound Chemical class 0.000 abstract description 3
- ZRZNJUXESFHSIO-UHFFFAOYSA-N Pleuromutilin Natural products CC1C(O)C(C)(C=C)CC(OC(=O)CO)C2(C)C(C)CCC31C2C(=O)CC3 ZRZNJUXESFHSIO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003674 animal food additive Substances 0.000 abstract 1
- 230000000536 complexating effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 37
- 238000002360 preparation method Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 7
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 6
- 229940097362 cyclodextrins Drugs 0.000 description 6
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 5
- 229960004853 betadex Drugs 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000001116 FEMA 4028 Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000282887 Suidae Species 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003651 drinking water Substances 0.000 description 3
- 235000020188 drinking water Nutrition 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000009918 complex formation Effects 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 208000001848 dysentery Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000006069 physical mixture Substances 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 125000003535 D-glucopyranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H] 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- OBUUFWIMEGVAQS-UHFFFAOYSA-N Pleuromutenol Natural products CC1C(O)C(C)(C=C)CC(O)C2(C)C(C)CCC31C2C(=O)CC3 OBUUFWIMEGVAQS-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000001202 beta-cyclodextrine Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012476 oxidizable substance Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 229960002771 retapamulin Drugs 0.000 description 1
- STZYTFJPGGDRJD-NHUWBDDWSA-N retapamulin Chemical compound C([C@H]([C@@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CS[C@@H]3C[C@H]4CC[C@H](N4C)C3)C)C[C@]32[C@H]1C(=O)CC3 STZYTFJPGGDRJD-NHUWBDDWSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010591 solubility diagram Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/76—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members
- C07C2603/80—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members containing eight-membered rings
- C07C2603/82—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members containing eight-membered rings having three condensed rings with in total fourteen carbon atoms and having a having a [5.4.3.0(1,8)] ring structure, e.g. pleuromutiline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0147791A AT400674B (de) | 1991-07-24 | 1991-07-24 | Pharmazeutische pleuromutilin-zubereitung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO922901D0 NO922901D0 (no) | 1992-07-22 |
| NO922901L NO922901L (no) | 1993-01-25 |
| NO300445B1 true NO300445B1 (no) | 1997-06-02 |
Family
ID=3514745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO922901A NO300445B1 (no) | 1991-07-24 | 1992-07-22 | Kompleks omfattende et pleuromutilinderivat og farmasöytisk preparat omfattende dette kompleks |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5578585A (pt) |
| EP (1) | EP0524632B1 (pt) |
| JP (1) | JP3296847B2 (pt) |
| KR (1) | KR100237719B1 (pt) |
| CN (1) | CN1039319C (pt) |
| AT (2) | AT400674B (pt) |
| AU (1) | AU656987B2 (pt) |
| BG (1) | BG61864B1 (pt) |
| BR (1) | BR9202804A (pt) |
| CA (1) | CA2074385C (pt) |
| CZ (1) | CZ281620B6 (pt) |
| DE (1) | DE69221793T2 (pt) |
| DK (1) | DK0524632T3 (pt) |
| ES (1) | ES2104775T3 (pt) |
| FI (1) | FI104788B (pt) |
| GR (1) | GR3025497T3 (pt) |
| HU (2) | HU214589B (pt) |
| IE (1) | IE80625B1 (pt) |
| IL (1) | IL102597A (pt) |
| MX (1) | MX9204318A (pt) |
| NO (1) | NO300445B1 (pt) |
| NZ (1) | NZ243662A (pt) |
| RO (1) | RO111680B1 (pt) |
| RU (1) | RU2099324C1 (pt) |
| SA (1) | SA92130137B1 (pt) |
| SG (1) | SG44633A1 (pt) |
| SK (1) | SK280773B6 (pt) |
| TW (1) | TW307770B (pt) |
| ZA (1) | ZA925600B (pt) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9614017D0 (en) * | 1996-07-04 | 1996-09-04 | Biochemie Gmbh | Organic compounds |
| UY25225A1 (es) | 1997-10-29 | 2000-12-29 | Smithkline Beecham Plc | Derivados de pleuromutilina utiles como agentes antimicrobianos |
| TWI260220B (en) * | 1999-11-22 | 2006-08-21 | Novartis Ag | A pharmaceutical composition for the transdermal treatment of bacterial infections in animals |
| US7052712B2 (en) * | 2001-10-05 | 2006-05-30 | Rubicon Scientific Llc | Animal feeds including actives and methods of preparing same |
| US6716448B2 (en) | 2001-10-05 | 2004-04-06 | Rubicon Scientific Llc | Domesticated household pet food including maintenance amounts of ivermectin |
| US6866862B2 (en) * | 2001-10-05 | 2005-03-15 | Rubicon Scientific | Animal feeds including heartworm-prevention drugs |
| CO5390081A1 (es) * | 2001-11-28 | 2004-04-30 | Novartis Ag | Compuestos organicos |
| GB0207495D0 (en) * | 2002-03-28 | 2002-05-08 | Biochemie Gmbh | Organic compounds |
| GB0218578D0 (en) * | 2002-08-09 | 2002-09-18 | Glaxo Group Ltd | Novel method |
| KR20040027191A (ko) * | 2002-09-27 | 2004-04-01 | 대한민국 (강원대학교) | 콜레스테롤이 감소된 알(卵)의 생산방법 |
| GB0308114D0 (en) * | 2003-04-08 | 2003-05-14 | Glaxo Group Ltd | Novel compounds |
| SI2260871T1 (sl) | 2004-04-01 | 2013-09-30 | Pierre Fabre Medicament | Kompleksi sestavin, ki vključujejo piroksikam, ciklodekstrin in arginin |
| EP1686115A1 (de) * | 2005-01-26 | 2006-08-02 | Novartis AG | Organische Säureadditionssalze von Valnemulin |
| EP1927615B2 (en) * | 2005-09-22 | 2020-03-25 | Toray Industries, Inc. | Polyarylene sulfide and process for production thereof |
| EP2159220A1 (en) * | 2008-09-02 | 2010-03-03 | Nabriva Therapeutics AG | Organic compounds |
| CN102266319B (zh) * | 2011-07-25 | 2012-11-28 | 武汉回盛生物科技有限公司 | 一种兽用盐酸沃尼妙林预混剂及其制备方法 |
| CN102764252A (zh) * | 2012-08-07 | 2012-11-07 | 湖北龙翔药业有限公司 | 一种盐酸沃尼妙林的用途 |
| US10532102B2 (en) | 2016-08-19 | 2020-01-14 | Foresee Pharmaceuticals Co., Ltd. | Pharmaceutical composition and methods of uses |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4092424A (en) * | 1964-04-17 | 1978-05-30 | Biochemie Ges.M.B.H. | Antibiotic derivatives |
| US4041175A (en) * | 1974-05-13 | 1977-08-09 | E. R. Squibb & Sons, Inc. | Use of pleuromutilin for the treatment of swine dysentery |
| US3987194A (en) * | 1975-05-12 | 1976-10-19 | E. R. Squibb & Sons, Inc. | Use of pleuromutilin derivatives for the treatment of swine dysentery |
| US4086359A (en) * | 1975-09-30 | 1978-04-25 | E. R. Squibb & Sons, Inc. | Derivatives of pleuromutilin and compositions |
| CH627940A5 (de) * | 1976-12-23 | 1982-02-15 | Sandoz Ag | Kokzidiostatisches kombinationspraeparat. |
| US4129721A (en) * | 1977-12-08 | 1978-12-12 | Eli Lilly And Company | A-40104 antibiotics and process for production thereof |
| US4130709A (en) * | 1977-12-08 | 1978-12-19 | Eli Lilly And Company | Pleuromutilin glycoside derivatives |
| CY1353A (en) * | 1979-01-12 | 1987-04-24 | Sandoz Ag | New pleuromutilin derivatives, their production and use |
| GB2072012B (en) * | 1980-03-14 | 1984-07-25 | Squibb & Sons Inc | Veterinary compositions containing pleuromutilin derivatives |
| JPS58148816A (ja) * | 1982-02-27 | 1983-09-05 | Nippon Zenyaku Kogyo Kk | 低刺激性チアムリン注射剤 |
| JPS58177949A (ja) * | 1982-04-12 | 1983-10-18 | Takeda Chem Ind Ltd | ランカシジン群抗生物質包接化合物 |
| JPS5910510A (ja) * | 1982-07-08 | 1984-01-20 | Nippon Zenyaku Kogyo Kk | 低刺激性チアムリン注射剤 |
| EP0153277B1 (de) * | 1984-02-17 | 1987-08-26 | Sandoz Ag | Neue Pleuromutilinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| JPS6191125A (ja) * | 1984-10-11 | 1986-05-09 | Nippon Zeon Co Ltd | Ｓ−アデノシル−ｌ−メチオニン含有組成物及びその製造法 |
| JPS62120344A (ja) * | 1985-11-20 | 1987-06-01 | Nippon Redarii Kk | ４−ビフエニリル酢酸エステル−シクロデキストリン包接化合物 |
| JPS62123196A (ja) * | 1985-11-22 | 1987-06-04 | Nisshin Flour Milling Co Ltd | プレドニゾロン包接化合物 |
| GB8613688D0 (en) * | 1986-06-05 | 1986-07-09 | Euro Celtique Sa | Pharmaceutical composition |
| JPS63139130A (ja) * | 1986-11-29 | 1988-06-10 | Nippon Funmatsu Yakuhin Kk | 長期安定型の漢方薬軟エキスの製造法 |
| JPH0819004B2 (ja) * | 1986-12-26 | 1996-02-28 | 日清製粉株式会社 | 徐放性医薬製剤 |
| JPS6463552A (en) * | 1987-09-04 | 1989-03-09 | Lederle Japan Ltd | 4-biphenylylacetic acid ester-cyclodextrin inclusion compound |
| CA1321192C (en) * | 1988-04-20 | 1993-08-10 | Abdul Majid | Inclusion complexes of cyclodextrins by agglomeration |
| US5007966A (en) * | 1988-09-21 | 1991-04-16 | American Maize-Products Company | Cyclodextrin complexing method |
-
1991
- 1991-07-24 AT AT0147791A patent/AT400674B/de not_active IP Right Cessation
-
1992
- 1992-07-13 HU HU9202307A patent/HU214589B/hu not_active IP Right Cessation
- 1992-07-22 BR BR929202804A patent/BR9202804A/pt not_active Application Discontinuation
- 1992-07-22 CA CA002074385A patent/CA2074385C/en not_active Expired - Fee Related
- 1992-07-22 NO NO922901A patent/NO300445B1/no not_active IP Right Cessation
- 1992-07-22 FI FI923342A patent/FI104788B/fi active
- 1992-07-22 AU AU20536/92A patent/AU656987B2/en not_active Ceased
- 1992-07-22 IL IL10259792A patent/IL102597A/en not_active IP Right Cessation
- 1992-07-22 BG BG96678A patent/BG61864B1/bg unknown
- 1992-07-22 NZ NZ243662A patent/NZ243662A/en unknown
- 1992-07-23 SG SG1996004628A patent/SG44633A1/en unknown
- 1992-07-23 CN CN92108688A patent/CN1039319C/zh not_active Expired - Fee Related
- 1992-07-23 CZ CS922311A patent/CZ281620B6/cs not_active IP Right Cessation
- 1992-07-23 SK SK2311-92A patent/SK280773B6/sk not_active IP Right Cessation
- 1992-07-23 EP EP92112634A patent/EP0524632B1/en not_active Expired - Lifetime
- 1992-07-23 MX MX9204318A patent/MX9204318A/es unknown
- 1992-07-23 DK DK92112634.8T patent/DK0524632T3/da not_active Application Discontinuation
- 1992-07-23 KR KR1019920013120A patent/KR100237719B1/ko not_active IP Right Cessation
- 1992-07-23 DE DE69221793T patent/DE69221793T2/de not_active Expired - Fee Related
- 1992-07-23 IE IE922392A patent/IE80625B1/en not_active IP Right Cessation
- 1992-07-23 JP JP19666592A patent/JP3296847B2/ja not_active Expired - Fee Related
- 1992-07-23 RO RO92-01019A patent/RO111680B1/ro unknown
- 1992-07-23 AT AT92112634T patent/ATE157260T1/de not_active IP Right Cessation
- 1992-07-23 RU SU925052221A patent/RU2099324C1/ru active
- 1992-07-23 ES ES92112634T patent/ES2104775T3/es not_active Expired - Lifetime
- 1992-07-24 ZA ZA925600A patent/ZA925600B/xx unknown
- 1992-07-25 TW TW081105891A patent/TW307770B/zh active
- 1992-09-30 SA SA92130137A patent/SA92130137B1/ar unknown
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1995
- 1995-03-10 US US08/402,272 patent/US5578585A/en not_active Expired - Lifetime
- 1995-06-30 HU HU95P/P00678P patent/HU211650A9/hu unknown
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1997
- 1997-11-26 GR GR970403146T patent/GR3025497T3/el unknown
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